1-(2-羟基-3,5-二硝基苯基)乙酮 | 69027-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-(2-羟基-3,5-二硝基苯基)乙酮
• 英文名称: 2'-hydroxy-3',5'-dinitroacetophenone
• 英文别名: 2-hydroxy-3,5-dinitroacetophenone；3,5-dinitro-2-hydroxyacetophenone；2-acetyl-4,6-dinitrophenol；1-(2-hydroxy-3,5-dinitro-phenyl)-ethanone；1-(2-Hydroxy-3,5-dinitro-phenyl)-aethanon；2-Hydroxy-3,5-dinitro-acetophenon；1-(2-Hydroxy-3,5-dinitrophenyl)ethan-1-one；1-(2-hydroxy-3,5-dinitrophenyl)ethanone
• CAS: 69027-37-8
• 化学式: C₈H₆N₂O₆
• 分子量: 226.145
• InChiKey: ZLYZQGCSKGCVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-3,5-二硝基苯基)乙酮 在 palladium on activated charcoal 硫酸 、 氢气 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， -78.0~110.0 ℃ 、275.79 kPa 条件下， 反应 44.0h， 生成 4',6,8-triaminoflavone
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src

  摘要：

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.

  DOI：

  10.1021/jm00046a020
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 硝酸 、 溶剂黄146 作用下， 生成 1-(2-羟基-3,5-二硝基苯基)乙酮
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src

  摘要：

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.

  DOI：

  10.1021/jm00046a020

文献信息

• Intramolecular electrophilic displacement of acyl by nitro group during attempted synthesis of 3-nitrocoumarins
  作者：George M. Benedikt、Lee Traynor

  DOI：10.1016/s0040-4039(01)80983-7

  日期：1987.1

  2-Hydroxyacetophenones undergo upon nitration in acetic acid a substitution of the acyl by nitro group followed by an intramolecular 1,3-acyl shift reminescent of a retro-Fries rearrangement to yield phenyl esters.

  2-羟基苯乙酮在乙酸中硝化后，酰基被硝基取代，然后分子内的1，3-酰基转移再发光，从而形成苯酯。
• Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides
  作者：Roger E. Ford、Phillip Knowles、Edward Lunt、Stuart M. Marshall、Audrey J. Penrose、Christopher A. Ramsden、Anthony J. H. Summers、Joyce L. Walker、Derek E. Wright

  DOI：10.1021/jm00154a019

  日期：1986.4

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.
• DE2846931
  申请人：——

  公开号：——

  公开（公告）日：——
• Da Re, Farmaco, Edizione Scientifica, 1956, vol. 11, p. 670,674
  作者：Da Re

  DOI：——

  日期：——
• Nitrohydroxy Aromatic Ketones. I. Nitrohydroxyacetophenones
  作者：Shiam Sunder Joshi、Hari Singh

  DOI：10.1021/ja01648a074

  日期：1954.10